Propanenitrile

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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas51.46kJ/molCcrHall and Baldt, 1971 

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid15.5kJ/molCcrHall and Baldt, 1971ALS
Quantity Value Units Method Reference Comment
Δcliquid-1948.3 ± 0.54kJ/molCcrHall and Baldt, 1971ALS
Δcliquid-1918.kJ/molCcbLemoult and Jungfleisch, 1909ALS
Quantity Value Units Method Reference Comment
liquid189.33J/mol*KN/AWeber and Kilpatrick, 1962DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
105.3298.15Mirzaliev, Shakhuradov, et al., 1987T = 193 to 353 K. Unsmoothed experimental datum given as 1.845 kJ/kg*K at 293 K. Cp(liq) = 1.9082 + 0.0027614T/K + 9.3056x10-6T2/K2 kJ/kg*K (193 to 353 K). Note, second term should be negative.; DH
106.0303.15Guseinov and Mirzaliev, 1985T = 303 to 363 K. p = 0.1 MPa. Unsoothed experimental datum given as 1.9250 kJ/kg*K.; DH
112.9297.Hall and Baldt, 1971DH
119.50298.15Weber and Kilpatrick, 1962T = 15 to 300 K.; DH

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tboil370. ± 1.KAVGN/AAverage of 31 out of 35 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus180. ± 7.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple180.37KN/AWeber and Kilpatrick, 1962, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc561.3KN/ACastillo-Lopez and Trejo Rodriguez, 1987Uncertainty assigned by TRC = 0.2 K; Visual, TE with digital voltmeter calibr. by meas. on alkanes.; TRC
Tc558.7KN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 2. K; TRC
Tc558.85KN/AGuye and Mallet, 1902, 2Uncertainty assigned by TRC = 1. K; TRC
Tc558.85KN/AGuye and Mallet, 1902, 2Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Pc42.60barN/ACastillo-Lopez and Trejo Rodriguez, 1987Uncertainty assigned by TRC = 0.10 bar; Visual; TRC
Pc41.80barN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 0.9119 bar; TRC
Pc41.7459barN/AGuye and Mallet, 1902, 2Uncertainty assigned by TRC = 0.8106 bar; TRC
Pc41.9485barN/AGuye and Mallet, 1902, 2Uncertainty assigned by TRC = 0.8106 bar; TRC
Quantity Value Units Method Reference Comment
Δvap36.3 ± 0.8kJ/molAVGN/AAverage of 6 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
36.116298.15N/AWeber and Kilpatrick, 1962P = 6.29 kPa; DH
31.81371.N/AMajer and Svoboda, 1985 
36.1303.AStephenson and Malanowski, 1987Based on data from 288. to 371. K.; AC
36.7326.BGBaldt and Hall, 1971Based on data from 308. to 363. K.; AC
36.5280.N/AMilazzo, 1956Based on data from 189. to 295. K. See also Boublik, Fried, et al., 1984.; AC
35.9323.N/ADreisbach and Shrader, 1949Based on data from 308. to 370. K. See also Dreisbach and Martin, 1949 and Boublik, Fried, et al., 1984.; AC

Entropy of vaporization

ΔvapS (J/mol*K) Temperature (K) Reference Comment
121.1298.15Weber and Kilpatrick, 1962P; DH

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
308.7 to 370.503.617321036.424-83.76Dreisbach and Shrader, 1949Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
5.03180.4Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
9.67177.0Domalski and Hearing, 1996CAL
27.91180.4

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.7067176.96crystaline, IIcrystaline, IWeber and Kilpatrick, 1962DH
5.0300180.37crystaline, IliquidWeber and Kilpatrick, 1962DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
9.64176.96crystaline, IIcrystaline, IWeber and Kilpatrick, 1962DH
27.89180.37crystaline, IliquidWeber and Kilpatrick, 1962DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
RCD - Robert C. Dunbar
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C3H4N- + Hydrogen cation = Propanenitrile

By formula: C3H4N- + H+ = C3H5N

Quantity Value Units Method Reference Comment
Δr1569. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1537. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C3H4N- + Hydrogen cation = Propanenitrile

By formula: C3H4N- + H+ = C3H5N

Quantity Value Units Method Reference Comment
Δr1640. ± 21.kJ/molG+TSMerrill, Dahlke, et al., 1996gas phase; comparable to H2O.; B
Quantity Value Units Method Reference Comment
Δr1607. ± 21.kJ/molIMRBMerrill, Dahlke, et al., 1996gas phase; comparable to H2O.; B

Sodium ion (1+) + Propanenitrile = (Sodium ion (1+) • Propanenitrile)

By formula: Na+ + C3H5N = (Na+ • C3H5N)

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
103.298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

Ethyl isocyanide = Propanenitrile

By formula: C3H5N = C3H5N

Quantity Value Units Method Reference Comment
Δr-90.0 ± 4.2kJ/molCmBaghal-Vayjooee, Collister, et al., 1977gas phase; Heat of isomerization; ALS

Henry's Law data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference
27. MN/A

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C3H5N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)11.85 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)794.1kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity763.0kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Reference Comment
0.015092 ± 0.000087Hammer, Diri, et al., 2003B

Ionization energy determinations

IE (eV) Method Reference Comment
11.5 ± 0.25EIChess, Lapp, et al., 1982LBLHLM
11.90PEKimura, Katsumata, et al., 1981LLK
11.85 ± 0.01PEStaley, Kleckner, et al., 1976LLK
11.85PELake and Thompson, 1970RDSH
11.84 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH2N+14.88?EIHeerma, deRidder, et al., 1969RDSH
C2H2+14.70?EIHeerma, deRidder, et al., 1969RDSH
C2H3+15.40?EIHeerma, deRidder, et al., 1969RDSH
C2H4+12.40 ± 0.05HCNEIFranklin, Wada, et al., 1966RDSH
C3H4N+13.00HEIHeerma, deRidder, et al., 1969RDSH
C3H4N+12.55 ± 0.05HEIFranklin, Wada, et al., 1966RDSH

De-protonation reactions

C3H4N- + Hydrogen cation = Propanenitrile

By formula: C3H4N- + H+ = C3H5N

Quantity Value Units Method Reference Comment
Δr1569. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr1537. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

C3H4N- + Hydrogen cation = Propanenitrile

By formula: C3H4N- + H+ = C3H5N

Quantity Value Units Method Reference Comment
Δr1640. ± 21.kJ/molG+TSMerrill, Dahlke, et al., 1996gas phase; comparable to H2O.; B
Quantity Value Units Method Reference Comment
Δr1607. ± 21.kJ/molIMRBMerrill, Dahlke, et al., 1996gas phase; comparable to H2O.; B

Ion clustering data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Sodium ion (1+) + Propanenitrile = (Sodium ion (1+) • Propanenitrile)

By formula: Na+ + C3H5N = (Na+ • C3H5N)

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
103.298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89

IR Spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass spectrum
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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 774
NIST MS number 227644

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Lemoult and Jungfleisch, 1909
Lemoult, M.P.; Jungfleisch, M.E., Thermochimie. - Comparaisons entre les nitriles et les carbylamines, Compt. Rend., 1909, 148, 1602-1604. [all data]

Weber and Kilpatrick, 1962
Weber, L.A.; Kilpatrick, J.E., Entropy and related thermodynamic properties of propionitrile, J. Chem. Phys., 1962, 36, 829-834. [all data]

Mirzaliev, Shakhuradov, et al., 1987
Mirzaliev, A.A.; Shakhuradov, Sh.G.; Guseinov, S.O., Investigation of the isobaric heat capacity of nitriles at different temperatures, Izv. Vyssh. Ucheb. Zaved., Neft i Gaz, 1987, 30(4), 55-58. [all data]

Guseinov and Mirzaliev, 1985
Guseinov, S.O.; Mirzaliev, A.A., Experimental investigation of volumetric and isobaric heat capacity of saturated nitriles at elevated temperatures and different pressures, Izv. Vyssh. Ucheb. Zaved., Neft i Gaz, 1985, 28(5), 58-62. [all data]

Weber and Kilpatrick, 1962, 2
Weber, L.A.; Kilpatrick, J.E., Entropy and related thermodynamic properties of propionitrile, J. Chem. Phys., 1962, 36, 829. [all data]

Castillo-Lopez and Trejo Rodriguez, 1987
Castillo-Lopez, N.; Trejo Rodriguez, A., The critical temperatures and pressures of several n-alkanenitriles, J. Chem. Thermodyn., 1987, 19, 671. [all data]

Guye and Mallet, 1902
Guye, P.A.; Mallet, E., Critical Constant and Molecular Complexity of Several Organic Compds., C. R. Hebd. Seances Acad. Sci., 1902, 133, 168. [all data]

Guye and Mallet, 1902, 2
Guye, P.A.; Mallet, E., Measurement of Critical Constants, Arch. Sci. Phys. Nat., 1902, 13, 274-296. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Baldt and Hall, 1971
Baldt, J.H.; Hall, H.K.K., Jr., Thermochemistry of strained-ring bridgehead nitriles and esters, J. Am. Chem. Soc., 1971, 93, 140-145. [all data]

Milazzo, 1956
Milazzo, G., Ann. Chim. (Rome), 1956, 46, 1105. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A., Vapor Pressure--Temperature Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054 . [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Merrill, Dahlke, et al., 1996
Merrill, G.N.; Dahlke, G.D.; Kass, S.R., beta-Cyanoethyl Anion: Lusus Naturae, J. Am. Chem. Soc., 1996, 118, 18, 4462, https://doi.org/10.1021/ja953796o . [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Baghal-Vayjooee, Collister, et al., 1977
Baghal-Vayjooee, M.H.; Collister, J.L.; Pritchard, H.O., The enthalpy of isomerisation of methyl isocyanide, Can. J. Chem., 1977, 55, 2634-2636. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Hammer, Diri, et al., 2003
Hammer, N.I.; Diri, K.; Jordan, K.D.; Desfrancois, C.; Compton, R.N., Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules, J. Chem. Phys., 2003, 119, 7, 3650-3660, https://doi.org/10.1063/1.1590959 . [all data]

Chess, Lapp, et al., 1982
Chess, E.K.; Lapp, R.L.; Gross, M.L., The question of tautomerism of alkylnitrile and isonitrile radical cations, Org. Mass Spectrom., 1982, 17, 475. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Staley, Kleckner, et al., 1976
Staley, R.H.; Kleckner, J.E.; Beauchamp, J.L., Relationship between orbital ionization energies and molecular properties. Proton affinities and photoelectron spectra of nitriles, J. Am. Chem. Soc., 1976, 98, 2081. [all data]

Lake and Thompson, 1970
Lake, R.F.; Thompson, H., The photoelectron spectra of some molecules containing the C N group, Proc. Roy. Soc. (London), 1970, A317, 187. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Heerma, deRidder, et al., 1969
Heerma, W.; deRidder, J.J.; Dijkstra, G., The electron-impact-induced fragmentation of n-alkyl cyanides, Org. Mass Spectrom., 1969, 2, 1103. [all data]

Franklin, Wada, et al., 1966
Franklin, J.L.; Wada, Y.; Natalis, P.; Hierl, P.M., Ion-molecule reactions in acetonitrile and propionitrile, J. Phys. Chem., 1966, 70, 2353. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), References